The film introduced the song "High Hopes" by Sammy Cahn and Jimmy Van Heusen, a Sinatra standard used as a campaign song by John F. Kennedy during the presidential election the following year.[4] Wynn plays a wealthy former friend of Sinatra's character who expresses interest in his plan to build a Disneyland in Florida (the film predates Disney World)—until he notices that Sinatra seems too desperate as he cheers for a dog upon which he'd bet heavily. The movie ends with Tony, Eloise and Alley singing "High Hopes" on the beach. Sinatra sings "All My Tomorrows," another Cahn/Van Heusen song, under the opening titles.

The screenplay was adapted by playwright Arnold Schulman, whose father was the operator of a Miami, Florida hotel. The protagonist of A Hole in the Head is a Miami hotel operator of "The Garden of Eden." The actual hotel used for the exterior shots was the Cardozo Hotel, located on Miami Beach's Ocean Drive. Shot over 40 days from 10 November 1958 to 9 January 1959, the film did not enjoy the smoothest of productions, especially during the location filming at Miami Beach. Sinatra's relations with the press were problematic, the media seizing on every anti-Sinatra rumor they could find.[5]

Aided by William Daniels, Capra completed the film a full 80 days ahead of schedule, its final production cost of $1.89 million well under the allotted budget. The film opened on June 17, 1959. Although having some positive reviews, the film was a modest box-office success, grossing $4 million in America.[5]

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Tony Manetta moved from the shabby area of the Bronx, New York to Miami, Florida with two friends, searching for wealth and success. One friend became prosperous over the next 20 years (owning luxury hotels) and is a promoter, while his younger friend drives a local taxi. Tony manages a small hotel called Garden Of Eden. He grew up poor but spoiled, spending money on expensive suits and a Cadillac, despite always being in debt and refusing to become more responsible. He is also a widowed father of an 11-year-old son named Alvin.

In debt, the rent five months in arrears, Tony is given 48 hours by his landlord, Abe Diamond, to raise $5,300 or else lose the hotel. Tony, in desperation calls his older brother Mario, who owns and operates a clothing store and has already loaned Tony money multiple times. Tony lies and says he needs a loan because Alvin is ill. Mario and wife Sophie promptly fly from New York City to Miami and discover the truth.

In Mario's eyes, Tony is a bum who wastes money on fanciful dreams rather than honest, hard work. He agrees to stake Tony the funds but only for a sensible small business, not dreams of fancy hotels or casinos. Mario also sets him up with Eloise Rogers, a widow and an acquaintance of Sophie, who is considered a more appropriate companion for Tony than his current girlfriend Shirl.

To his surprise, Tony is impressed with Eloise. His son Alvin also takes an immediate liking to her. Mario offends her, however, with prying questions about her late husband's will and finances, causing Tony to confess why they were introduced. Eloise reveals to Tony that having lost both her husband and son, she appreciates the notion of being with someone who needs her.

The old childhood pal, Jerry Marks, now a wealthy promoter, invites Tony to a party. Pretending to be prosperous, Tony explains his scheme to buy land in Florida and open a second Disneyland there. Jerry seems interested in being his partner again.

He takes Tony to a greyhound racing track, where Tony uses the $500 he earned from selling his Cadillac to match Jerry's large bet. His dog wins, but he lets it ride in the next race on a dog called Lucky Ally. The obvious desperation in Tony's voice as he roots for the dog to win indicates to Jerry that he is not a man of means. Jerry chastises him afterwards and tries to brush him off by insultingly handing him some cash. When Tony throws the cash handout back in Jerry's face, Tony is punched by one of Jerry's bodyguards.

Literally a beaten man, Tony decides it would be best if Alvin lived in New York with Mario and Sophie, telling the unconvinced boy that he is unwanted. Tony goes off to the beach by himself, but Alvin finds him, and soon Eloise happily joins them. Mario and Sophie decide to take a long, overdue vacation.

The film was based on the Broadway play of the same name.[5] It debuted at the Plymouth Theatre on Broadway on February 28, 1957 and featured actor Paul Douglas in the lead role. The play earned a Tony Award for Boris Aronson in 1958 for Best Scenic Design. On July 13, 1957, the show closed for a total of 156 performances.[6][7] Sinatra's agent, Bert Allenberg, bought the film rights for $200,000.[5]